Grimm held the NY-11 district seat until 2015, when he was imprisoned for federal tax fraud. Donovan sailed in with a special election victory to save face for the party. Now Grimm wants the seat back.

Donovan, the former Staten Island district attorney, is the establishment pick, scoring endorsements from most of the Empire State’s GOP old guard, the National Republican Congressional Committee, former New York City Mayor Rudy Giuliani (R), and, most critically, President Trump. But Grimm remains popular in the heavily ethnic white, GOP-leaning district that takes in all of Staten Island and a stretch of south Brooklyn. And in spite of Trump’s endorsement of Donovan, Grimm has campaigned hard as the true Trumpian candidate.

Thanks to Grimm’s surprisingly strong standing with a chunk of the district’s Republicans, the state’s arcane election laws and the race’s uncertain Trump factor, Grimm has a good shot at pulling the whole thing off. But New York Republicans fear that his significant baggage could imperil their hold on a seat that Donovan should be able to win in the fall.

“If Grimm wins, it’ll be a tough fight and yes, the Republicans can lose that seat,” del Percio, who worked for Grimm in his 2010 primary campaign and never worked with Donovan, continued. “You have a vulnerable, deeply flawed candidate who is a convicted felon. That’s something you can raise a lot of money against and really go after to increase turnout this election cycle.”

Another New York Republican consultant, who asked to remain anonymous because of his ties to both GOP candidates, said Democratic frontrunner Max Rose “has a chance” in the general, especially because Trump’s endorsement for Donovan came so late in the race.

“If Donovan loses, it signals Trump can’t boost support for the only Republican in his entire home city of New York” the consultant said.

After all, the conservative firebrand was best remembered for two events: his on-camera threat to break a NY1 reporter in half “like a boy,” and his 2014 felony criminal trial for fraud, tax evasion and perjury.

Donovan’s camp shrugged the challenge off, pointing to Grimm’s less-than-hard-right voting record in Congress and criminal record. They set about securing mainstream endorsements and raising funds.

Grimm, meanwhile, hit the campaign trail hard, turning out for parades, knocking on doors and snapping photos with white-haired grandmothers. He brought Trump allies including Michael Caputo and Anthony Scaramucci into the fold, and gave frequent press interviews casting himself as the strongest champion of the #MAGA agenda.

STATEN ISLAND, NEW YORK – MAY 28: Former Republican congressman and convicted felon Michael Grimm campaigns for his old seat. (Photo by Andrew Lichtenstein/Corbis via Getty Images)

“Donovan I think was overconfident for a long, long time,” Gerry O’Brien, a 40-year veteran of New York GOP politics who left the party during the 2016 election, told TPM.

O’Brien said the Donovan campaign made a “strategic blunder” by telegraphing their central attack on Grimm’s voting record months before the election, when “regular voters were paying less than zero attention.”

All the strategists TPM spoke to voiced similar concerns: Donovan was a lackluster retail campaigner while Grimm excelled at it; Donovan squandered his financial advantage on dull direct mail buys; Donovan didn’t take Grimm seriously until late in the race.

The national GOP has been worried about the race for some time. The NRCC added Donovan to their “Primary Patriots” program, providing additional fundraising and organizing assistance. While the NY1 poll was still being conducted, the president came out with a two-tweet endorsement for the incumbent warning what might happen if Grimm wins the nomination.

The Grimm campaign claims Trump was hoodwinked into supporting Donovan, noting that his first tweet claimed the congressman supported the tax cut bill that Donovan actually voted against.

“Donovan has abandoned a district that voted overwhelmingly for Trump,” Ryan Girdusky, a strategist providing support to Grimm’s primary campaign, told TPM. “Michael Grimm will be their advocate in Congress.”

Grimm has made his own mistakes. One notable misstep involved New York’s arcane election rules, which allow candidates to file signatures with the Board of Elections to appear on multiple party ballot lines. A Grimm campaign operative messed with the signatures Donovan’s team submitted, trying to keep him off the Reform Party ballot.

But he was caught, and the BOE not only kept Donovan on the Reform Party line but referred the incident to the U.S. Attorney’s office.

There were other allegations of dirty tricks. Donovan accused Grimm of filing an ethics complaint against him, claiming that Donovan helped his partner’s son secure preferential treatment after a 2015 heroin arrest. (Grimm denies making the complaint, while Donovan denies intervening).

STATEN ISLAND, NEW YORK – MAY 28: Republican congressman Dan Donovan marches with his family in Staten Island’s 100th Memorial Day Parade. (Photo by Andrew Lichtenstein/Corbis via Getty Images)

At a primary debate last week, Grimm charged that Donovan even sought to secure a presidential pardon on his behalf in order to keep him out of the primary race. Donovan acknowledged discussing the prospect of a pardon while riding on Air Force One with Trump last summer, but said he only did so as a favor to a longtime friend in Staten Island politics who’s now backing Grimm, former Rep. Guy Molinari (R-NY).

Donovan’s team counters that this is just another bogus accusation made by a campaign thrown into disarray by Trump’s endorsement, which upended the dynamics of the race.

“Grimm’s entire campaign was built around President Trump, who urged voters not to vote for him and said literally no one is better to represent him than Donovan,” Donovan spokeswoman Jessica Proud scoffed on a call with TPM.

With the primary just days away, Grimm is continuing to make Donovan’s electability argument for him.

Grimm caught flak in the conservative New York Post this week for downplaying an audio recording of distraught immigrant children separated from their parents by the Trump administration. Grimm told reporters, “You’re going to hear the same exact things as a mother leaves to go to work and has to leave her child at day care.”

The GOP strategist who requested anonymity said Grimm was “basically writing a Democratic campaign ad” with his comments.”

Rose, the leading Democratic candidate and a decorated U.S. Army veteran, has pulled in hundreds of thousands of dollars in donations and scored endorsements from the likes of the DCCC, Sen. Kirsten Gillibrand (D-NY), and the Service Employees International Union.

Kevin Elkins, Rose’s campaign manager, told TPM they’re “feeling pretty confident” about the race regardless of their opponent, but said they’d prefer to face off against Grimm because they would relish defeating him “once and for all.”

As Elkins pointed out, the peculiarities of New York’s ballot system means “this could go thirty different ways.”

Candidates are permitted to remain on multiple party lines even after losing a major-party primary. So either Grimm or Donovan could lose the Republican primary and stay on the November ballot on a minority-party line, peeling votes away from their rival.

O’Brien, the former GOP strategist, predicted Tuesday’s results will be closer than polls have shown, citing Trump’s support and Donovan’s last-minute assault of TV advertising.

“Whether that’s enough, I don’t know,” he said. “The Republican Party has jumped off the cliff in a very enthusiastic display of suicide over the last year or two. It would not be uncharacteristic for them to have gone all in on this and still throw another congressional seat away.”

Allegra Kirkland (@allegrakirkland)
Allegra Kirkland is a New York-based reporter for Talking Points Memo. She previously worked on The Nation’s web team and as the associate managing editor for AlterNet. Follow her on Twitter @allegrakirkland.